Potassium Carbonate → 1-[2-(4-Hydroxy-3-fluorophenoxy)ethyl]-4-(4-methylbenzyl)piperidine hydrochloride
Reaction equation
[ClH:1].[CH3:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1.C([O:23][C:24]1[CH:33]=[CH:32][C:27]([O:28][CH2:29][CH2:30]Br)=[CH:26][C:25]=1[F:34])C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>>[ClH:1].[OH:23][C:24]1[CH:33]=[CH:32][C:27]([O:28][CH2:29][CH2:30][N:11]2[CH2:12][CH2:13][CH:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([CH3:2])=[CH:15][CH:14]=3)[CH2:9][CH2:10]2)=[CH:26][C:25]=1[F:34]Participants
4
Procedure
The title compound was prepared from 4-(4-methylbenzyl)piperidine hydrochloride (347 mg, 1.54 mmol), 2-(4-benzoxy-3-fluorophenoxy)ethyl bromide (499 mg, 1.54 mmol) and potassium carbonate (531 mg, 3.85 mmol) in two steps as white-off solid (272 mg): mp 148-150° C. 1H NMR (CD3OD) 1.38 (m, 2 H), 1.699 (m, 3 H), 2.100 (s, 3 H), 2.375(d, J=6.3 Hz, 2 H), 2.834 (m, 2 H), 3.307 (m, 2 H), 3.427 (d, J=11.7 Hz, 2 H), 4.078 (t, J=4.8 Hz, 2 H), 6.48 (m, 1 H), 6.638 (m, 2 H), 6.844 (m, 4 H). Anal. Calcd for C21H27ClFNO2.0.3H2O: C, 65.45; H, 7.22; N, 3.64. Found: C, 65.54; H, 7.15; N, 3.60.
Sources & evidence
- ORD record
- ord-ef21a1645f3a4163b296343a873eb661
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06124323
Reaction notes
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